Insecticides
Frank A. Barile in Barile’s Clinical Toxicology, 2019
The mechanism of toxicity, however, differs slightly from that of the OP compounds. Table 28.2 summarizes the chemical properties and toxic animal data of some popular carbamate insecticides. Figure 28.2 illustrates the functional substitutions of two carbamate compounds from the carbamate parent molecule. Substitution of the N-isopropylthiol group and the heterocyclic phenyl constituents for R′ on the parent carbamate molecule on aldicarb and carbaryl, respectively, accounts for the decrease in toxicity (Table 28.2) seen with these insecticides. Structures of carbamate parent molecule and selective carbamate compounds are illustrated. Blue highlight indicates structural similarities retained from the parent molecule.
Rationale and technique of malaria control
David A Warrell, Herbert M Gilles in Essential Malariology, 2017
Classified by their chemical characteristics, the most common insecticides applied in public health practice are: petroleum oils and their derivatives;active constituents of flowers of pyrethrum (pyrethrins) or some newer synthetic compounds of this group (pyrethroids);chlorinated hydrocarbons: dichloro-diphenyl-trichloroethane (DDT), hexachlorocydohexane (HCH) and dieldrin;organophosphorous insecticides: malathion, temephos etc.;carbamates: propoxur, carbaryl etc.;insect growth regulators: diflubenzuron, methoprene, pyriproxyfen.
Management of Natural Rubber Glove Sensitivity
Robert N. Phalen, Howard I. Maibach in Protective Gloves for Occupational Use, 2023
Unlike the ICD, the lesions of ACD tend to extend beyond the site of contact. Pruritus is usually intense. The risk of NRL-related ACD is high in healthcare workers, hairdressers, cleaners, food handlers, food processing industry workers, and construction workers.20–22 A history of atopic dermatitis/atopy and a longer duration of glove use are additional risk factors.23,24 In Sweden, contact allergy to rubber additives was significantly common in HCWs with hand eczema compared to HCWs without hand eczema (6% vs 1%). Occupational contact allergy to rubber additives was significantly related to sick leave in the same study population.24 A study from Italy has demonstrated an increased risk of sensitization to carbamates and thiurams in HCWs. Thiuram sensitivity was also associated with dermatitis in restaurant workers, hairdressers, construction workers, and mechanics.25
Metabolism and in vitro drug–drug interaction assessment of viloxazine
Published in Xenobiotica, 2020
Distinct from reactive acyl glucuronides, N-carbamoyl glucuronide conjugates have not been reported to be associated with any adverse events. This is almost certainly a consequence of the relative stability of the conjugate. The stability of the conjugate is inherent in the carbamate moiety, which allows delocalization of electron density through the ester and amide portion of the carbamate (Ghosh & Brindisi, 2015). The carbamate group is a key structural motif in many approved drugs and prodrugs because of its stability and resistance to hydrolytic and proteolytic cleavage as well as other desirable properties (Ghosh & Brindisi, 2015). Although the use as a prodrug does require carbamate cleavage, this reaction is almost always carried out by a specific esterase and not mediated by endogenous nucleophiles. An example of the stability of a typical N-carbamoyl glucuronide can be seen in a study by Gunduz et al. (2010) where β-glucuronidase efficiently cleaved the conjugate to yield the parent; however, the conjugate was completely stable in the control incubation (buffer at 37 °C for 4 h). Problematic acyl glucuronides typically have buffer half-lives of <2 h (Gunduz et al., 2018).
Studies on oral subacute toxicity of cartap in male mice
Published in Drug and Chemical Toxicology, 2021
Laxman P. Sharma, Mayur P. Kadve, Madhu C. Lingaraju, Avinash G. Telang
Though cartap toxicity has been considered to be minimal, carbamates have been reported to have high mammalian toxicity, and the main target organs are brain, liver, skeletal muscles, and heart (Gupta 1994, Risher et al. 1987). In addition, kidney and reproductive functions have been reported to be adversely affected with carbamate exposure to rats (Kareem et al. 2007, Bindali and Kaliwal 2002). Cartap-induced cellular death in C2C12 cell line of mouse skeletal muscle has been shown to be mediated by generation of reactive oxygen species (ROS) (Liao et al. 2006). Antioxidant systems neutralize ROS and reduce their damaging abilities but when there is any imbalance in oxidant and internal antioxidant defense mechanism oxidative stress will result which causes lipid peroxidation, cross linking of DNA and protein (Romero et al. 1998). Carbamates are also known to cause significant changes in total serum lipids, glucose, protein levels, AST, ALT, acid phosphatase and alkaline phosphatase activities in mammals (Sadek et al. 1989, Fayez and Kilgore 1992, Chevalier et al. 1993). However, there are no known reports available on mid- or long-term toxic effects of cartap, a thiocarbamate in animal models. Therefore, the present study was carried out to investigate the effects of cartap on oxidative stress and histopathological alteration in vitals like liver, kidney, and brain of mice after 28 days oral exposure.
Investigation of pesticides on honey bee carbonic anhydrase inhibition
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2020
Ercan Soydan, Ahmet Can Olcay, Gürkan Bilir, Ömer Taş, Murat Şentürk, Deniz Ekinci, Claudiu T. Supuran
The two carbamates from Figure 1, methomyl, and oxamyl can be substrates of CAs which may hydrolyse their ester/thioester bonds with the formation of small molecules which can bind to the metal centre (acetate, methyl-thiol, or Me2N–COCOOH in the case of the second carbamate). The pyrethroids may also be hydrolysed at their ester functionality, with the generation of carboxylic acids and alcohols which were shown to act as CAIs12,13,36. Diazinon has thiophosphate functionalities which were shown to be hydrolysed by the esterase activity of CAs in previous work from this laboratory, leading to suicide inhibitors of the enzyme39. However, these hypotheses should be verified by X-ray crystallography, one of the most powerful techniques useful to assess CA inhibition mechanisms, especially the innovative ones. This technique also has its weak points, especially when used in an inattentive manner. The best example is the report by Liljas’ group that cyanide and cyanate do not coordinate the metal ion from CA active site44. Subsequent work from other laboratories showed those data to be false, as both cyanate and cyanide were observed coordinated to the metal ion, as most other anion inhibitors investigated to date45,46. Furthermore, cyanate was also shown to be a suicide substrate that can be hydrolysed by the CA activity with the formation of carbamate45. However, bitter and dubious comments from the above-mentioned crystallography group continued even 30 years later47.
Related Knowledge Centers
- Carbamic Acid
- Chemical Structure
- Ester
- Functional Group
- Organic Chemistry
- Organic Compound
- Chemical Formula
- Ethyl Carbamate
- Hydrogen
- Salt